The Watson Weekly: eCommerce Strategy & News

Watson Weekly
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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

  1. 1D AGO

    February 23rd, 2026: Stripe’s $140 Billion Question, Why Temu is the New Cross-Border Standard, The UPS $150k Exit: Strategic Rightsizing or a Teamster Trap? and Is Agentic Commerce a Nothingburger?

    Today on our show: Stripe’s $140 Billion QuestionWhy Temu is the New Cross-Border StandardThe UPS $150k Exit: Strategic Rightsizing or a Teamster Trap?Is Agentic Commerce a Nothingburger? The Agentic Debate Series, presented by Logicbroker. - and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs. Today's episode is sponsored by Mirakl. https://www.watsonweekly.com/ https://www.youtube.com/@WatsonWeekly https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

    14 min

  2. 4D AGO

    She Broke The Saks Global Saga

    This week on the Watson Weekly Weekend edition, Rick Watson and Jessica Lesesky are breaking down a massive shift in the retail and tech landscape. From the dramatic fall of a luxury giant to Walmart's historic milestone and the high-stakes risks facing Silicon Valley’s finest, we’ve got the insights you need to stay ahead. In This Episode🎭 As the House of Luxury Turns: The Saks Global SagaWe track the "episodic drama" of Saks Global’s decline, from unpaid vendors and empty shelves to the January Chapter 11 filing. We dive into the friction with Amazon and the aggressive store closures impacting Saks Off Fifth and Neiman Marcus. 🛒 Walmart’s $1 Trillion MilestoneWalmart has officially joined the elite tech-heavy $1T market cap club. We discuss how their massive investments in supply chain automation and a "dot-com culture" (thanks to the legacy of Jet.com) are now allowing them to outpace Amazon’s e-commerce growth. 📦 FedEx: Better, Not BiggerFedEx is pivoting away from "tiny cheap shipments" to focus on high-margin sectors like healthcare and aerospace. We look at their Network 2.0 strategy and how they are navigating the rise of de minimus shipments from players like Shein and TikTok Shop. +⚠️ The Existential Risks of Big Tech What keeps CEOs up at night? We identify the "one big risk" for the giants: Amazon: Will the $200B AI backlog actually materialize?Shopify: Is a "high-performance sports team" culture sustainable for a 100-year company?Meta: The massive bet on "face computers" and ongoing legal distractions.OpenAI: The "show me the money" moment and the lack of native distribution. #Retail #Ecommerce #Walmart #SaksGlobal #FedEx #BigTech #Amazon #SupplyChain #WatsonWeekly

    26 min

  3. 6D AGO

    Mythbusting AI: Why SaaS Isn't Dead and Your Job Might Be Safer Than You Think

    Is SaaS really dead? Will AI take your job next year? In this Watson Weekly Interview, Rick Watson talks with Dr. Daniel Hulme, Chief AI Officer at WPP and CEO of Satalia, to debunk the biggest myths surrounding Artificial Intelligence. From the changing architecture of software to the rise of "Economic Singularity," Dr. Hulme provides a masterclass on how businesses and individuals can navigate the rapidly evolving tech landscape. We dive deep into: The Future of SaaS: Why LLMs are amplifying—not killing—software.The WPP Open Strategy: How AI unlocked creativity and content creation at scale.Why AI Projects Fail: From "intoxicated graduate" syndrome to the trap of low-hanging fruit.The Job Market: Transitioning from economic disruption to a world of abundance and UBI.GSO (Generative Search Optimization): Move over SEO—learn how to brand your business inside the "brains" of LLMs. Whether you are a SaaS founder, a marketer, or simply curious about the future of humanity, this conversation offers a grounded, expert perspective on the AI revolution. Chapters0:00 - Introduction to Dr. Daniel Hulme2:15 - Myth: Is SaaS Dead?5:40 - The 3-Layer Architecture of Modern Software8:20 - How WPP Open uses AI for Creative & Content12:45 - 5 Reasons Your AI Initiative Will Fail18:30 - AI vs. Jobs: The Path to Economic Singularity23:10 - Universal Basic Income and the Future of Work26:50 - Introduction to Generative Search Optimization (GSO)30:00 - Closing Thoughts: Living Your "True Humanity" #AI #SaaS #FutureOfWork #WPP #MachineLearning #GenerativeAI #TechTrends

    27 min

  4. FEB 16

    February 16th, 2026: Amazon is a Vertically Integrated Utility, Shopify Fiscal Year 2025 Earnings: a Pony with One Great Trick, Could it Be More? Kroger Opens a New Marketplace, and Paypal Earnings and David Marcus

    Today on our show: Amazon is a Vertically Integrated UtilityShopify Fiscal Year 2025 Earnings: a Pony with One Great Trick, Could it Be More?Kroger Opens a New MarketplacePaypal Earnings and David Marcus - and finally, The Investor Minute, which contains 5 items this week from the world of venture capital, acquisitions, and IPOs. Today's episode is sponsored by Mirakl. https://www.watsonweekly.com/ https://www.youtube.com/@WatsonWeekly https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

    16 min

  5. FEB 13

    Shopify: It’s Always Been About the Checkout and Swipe Stupid

    Welcome to the Watson Weekly Weekend Edition. Hosts Rick Watson and Jessica Lesesky dive into the post-Super Bowl landscape to break down the biggest moves in retail, tech, and AI. From the high-stakes world of $7 million for 30 second ads at the big game to the massive earnings reports from industry titans (hello Amazon), we’re unpacking what these shifts mean for the future of commerce. In This Episode:The AI Ad Wars: We review the ads from the big game spots from Claude (Anthropic), OpenAI, and Gemini. Is Anthropic just throwing shade at competitors, or is there a method to the "negative ad" madness? Target’s Executive Carousel: Target is shuffling the deck chairs again. With a new CEO and a history of moving merchants into marketing roles, we ask: why does Target seem "allergic" to a real CMO? Spotify vs. Amazon (The Book Edition): In a surprising move, Spotify is partnering with Bookshop.org to sell physical books. We explore why they’re helping independent bookstores while indie artists feel left behind. Amazon Earnings Deep Dive: AWS is back on "high-speed rail" growth, and the new AI assistant Rufus is already driving billions in sales. Plus, we discuss the genius of the "add to delivery" feature. Shopify’s AI Strategy: Shopify is growing at nearly 30% a year, but investors have one question: What is the AI strategy? Rick explains why Shopify’s "one trick"—the checkout—is still their greatest strength. The Watson Weekly Weekend Edition is sponsored by Mirakl: Powering the next era of retail. Video Timestamps0:00 - Welcome to Watson Weekend 0:54 - The Big Game Ad Economics: $233,000 Per Second 2:18 - The AI Ad Wars: Anthropic (Claude) vs. OpenAI 3:56 - Google Gemini’s "Heartstrings" Ad Campaign 5:14 - Target’s Leadership Shuffle: Why the "Roach Motel" Strategy? 8:17 - Spotify’s Strange Pivot into Physical Books 9:54 - The Indie Artist Royalty Gap which Should Make Publishers Worried 11:13 - Amazon Earnings: AWS High-Speed Growth & Rufus+2 13:06 - Amazon’s New "Add to Delivery" Feature 14:26 - The Future of Amazon Grocery & Whole Foods 15:05 - Shopify Earnings: B2B and International Growth 16:51 - Shopify’s AI Narrative: "It's the Checkout, Stupid" 19:54 - Final Thoughts Stay Bold. Stay Classy Subscribe to our Newsletter: watsonweekly.com and YouTube channel.

    23 min

  6. FEB 11

    Why Your Agency is Falling for the AI Trap

    In this episode, host Rick Watson is joined by Mark Rubin, CEO of Kasama, to cut through the noise of the current agency landscape. Mark brings decades of experience from his time at Lyons Consulting, Precision Design Studios, and Moku Collective to discuss why the "AI Gold Rush" might be a trap and why replatforming your e-commerce site might be a mistake in 2026. In this episode, we discuss: The PE Cycle: Mark’s firsthand experience with private equity acquisitions and the "ticking clock" that begins once the checks clear.The AI Trap: Why clients are demanding AI provisions in contracts and how it’s creating a "margin pressure" that forces agencies to move from deliverables to results-based models.Hiring in the AI Era: The challenges of vetting developers who use AI tools and why "hiring slow and firing fast" is more important than ever.To Replatform or Not?: Mark’s controversial take on why brands should maximize their current tech stacks rather than chasing a "sexy" new platform that may result in a massive internal distraction. 🕒 Timestamps:0:00 – Introduction: Cutting through the Agency Noise 2:15 – Mark’s Journey: From .NET Developer to CEO 5:30 – The Reality of Private Equity and "The Clock" 9:45 – Is the AI Gold Rush a Trap for Agencies? 14:20 – The Evolution of Agency Pricing: Time & Materials vs. Results 18:10 – Why You Probably Shouldn’t Replatform This Year 22:45 – Closing Thoughts: Focus on the Basics #watsonweekly #watsonweeklyinterview #agency #ai #replatform

    25 min

  7. FEB 9

    The Goliath Paradox: Why Scale is a Lie in Modern Commerce

    The Watson Weekly podcast, sponsored by Rithum, presents the keynote speech delivered in New York City on Sunday, January 11th, prior to the National Retail Federation Big Show. The. Watson Weekend Live at NRF Presented by Radial, keynote speech focused on "being bold in 2026.” The core idea is the "Goliath paradox," which argues that while David won, businesses often forget why Goliath lost. Rick Watson contends that the belief that "scale is safety" is a "lie," and in today's economy, the only real "moat is actually motion" because "size without motion is just a target". Larger companies risk slowing down, becoming heavy and slow like Goliath, who couldn't dodge the rock. The current era is the "age of intelligence," demanding that brands not just respond to demand but "anticipate demand before it even comes". The speaker uses Lululemon versus Alo and Victoria's Secret versus Skims as examples of bold challengers. In the case of Skims, the brand won by selling "the combination of high fashion engineering and body positivity," meeting customers "exactly where they are," while Victoria's Secret sold a fantasy. The ultimate challenge for 2026 is that brands need to compete on identity and "stand for something". The choice is between being a "giant who can't move" (a path of paralysis and incrementalism) or the "giant who learned how to dance," driven by a mindset of "speed, agility, and most importantly, adaptability". The Watson Weekly podcast is sponsored by Rithum. In commerce, every second counts. Rhythm helps brands and retailers connect every channel with AI-powered automation and insights, giving you the clarity to make smart decisions, adapt fast, and grow efficiently. Learn more at tithum.com. That's R-I-T-H-U-M.com. If you find conversations like this helpful, make sure you’re following the show so you don’t miss future episodes. Also, if you’re not subscribed to our newsletter, check that out at www.watsonweekly.com.

    24 min

  8. FEB 6

    Whatnot vs Traditional E-commerce: The Shift No One’s Talking About

    Join your Watson Weekly Weekend Edition hosts, Rick Watson and Jessica Lesesky, as they break down the biggest shifts in tech, retail, and e-commerce. From Pinterest’s AI pivot to Starbucks’ massive loyalty shakeup, we’re diving deep into the news moving the needle this week. 📌 Pinterest’s AI EvolutionPinterest is cutting 15% of its workforce (approx. 700–800 roles) to go all-in on AI. We discuss whether this is a genuine transformation or a "playbook" move to appease investors as user growth plateaus. Is the shift to "AI-proficient talent" enough to fend off TikTok and Reels? ☕ The New Starbucks Rewards (Launching March 10, 2026)Starbucks is reimagining loyalty with three distinct tiers designed to gamify your morning coffee: Green: The standard $1 = 1 star.Gold: Accelerated earning (1.2 stars/$) and non-expiring points.Reserve: A 2,500-star threshold (or $2,500 spend) with perks like all-expenses-paid trips to Tokyo, Milan, or Costa Rica.Note: The "free customization" era is ending with a new $10 cap on 200-star drinks.🛍️ Shopify vs. The "Robot Agents" Shopify’s latest partner update provides a blueprint for the AI era. They are redefining "partners" to include digital entities and tightening the reins on data—prohibiting developers from using merchant data to train external models. Plus, third-party apps must now feed directly into the Shopify AI Sidekick. 🃏 Whatnot & The Live Selling ExplosionLive shopping has evolved far beyond QVC. Whatnot has reached $8 billion in GMV by gamifying the collector experience. We explore why midsize cities like Rochester and Dayton are out-earning Chicago on a per-resident basis, and how categories like Beauty (up 791%) are exploding. "It’s not shopping; it’s entertainment." – Special Correspondent Shephard Lesesky on the addictive nature of live auctions. The Watson Weekly is sponsored by Mirakl. 0:00 – Intro 1:25 – Pinterest’s Strategic Pivot 5:31 – Starbucks Loyalty 2026 8:58 – Shopify’s New Rules 13:15 – The Rise of Whatnot 🚀 Stay Connected Subscribe to our podcast and YouTube channel for your weekly dose of commerce insights. Visit our website: https://www.watsonweekly.com #WatsonWeekly #EcommerceNews #StarbucksRewards #Shopify #Pinterest #LiveShopping #Whatnot #AI #RetailTrends

    24 min
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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

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